Below are a few coaching tips to increase the learning opportunities when riding along with sales reps for observation:

• Always debrief at the end of the day or in the car on the way to the next appointment, and most importantly be absolutely sure the client is out of earshot.  It can be very discouraging and detrimental to a potential deal for a client to hear you critiquing and coaching the rep.
• There will certainly be things you will uncover that your rep must work on.  However, don’t lay them all out on the table at once as this could be overwhelming.  Present only 2-3 ideas or potential areas of improvement, and make notes of others to be brought up at a later date.  Bringing up 16 issues is a good way to get your rep to go on the defensive and shut down.  Plus, realistically even the quickest learners can only effectively work on a few issues at a time while producing real results.
• Do unto others as you would like them to do unto you.  Speak, coach, and encourage your rep in the same ways you would want a manager to do for you.
• Keep your distance, you are there to help, but most importantly to observe.  Resist the urge to try and step in often and try to “save” every opportunity.  This takes control of the situation and credibility away from the rep.  Should any opportunities be lost, treat it as a great learning opportunity for you to coach them on.  Real world scenarios are the best teachers.